Education has been an evolving enterprise since Plato first sat at Socrates' feet. What sets the past few decades apart in the history of education, though, is the rapid pace of change. New technologies, workforce demands, consumer expectations, entrepreneurial innovations and public sensitivity to cost are increasing the pressure for accessible, productive and meaningful education programs. Yet, too often, traditional higher education policies and financial aid rules stymie even the most sensible of these innovations. Federal aid programs were designed primarily around traditional semester, quarter or longer-term certificate calendars. In past years, Congress and the U.S. Department of Education (ED) have tweaked around the edges to accommodate online and modular modalities. In more recent years, ED has used its experimental sites authority to study potential regulatory changes to foster innovation in competency-based education, subscription models, short-term certificates and partnerships with non-traditional education providers. Yet, existing ED guidance and the potential of non-compliance liability continues to stifle innovation and wider use of emerging educational concepts and technologies. The barriers include anachronistic regulations and practices which, while well-intentioned, cause institutions to shy away from innovation. This report addresses these barriers with recommendations that both expand ED's tool set to foster innovation and revise regulations to better support emerging educational programs and maintain adequate protections for students and taxpayers.